3 Super Awkward Dating Moments (and How to Handle Them!)

Awkward moments aren’t so awkward if you expect them, or decide in advance how to handle them. Life is all about being prepared! There are a few situations you may incur in dating that can make for extremely uncomfortable moments. First, however, let’s discuss the reasons why awkward moments are so awkward.

Awkward situations in dating are uncomfortable largely because you don’t know the other person. You have no idea what they’re thinking, how they’re truly feeling, or what they’re expecting. Your self image and degree of guilt-proneness are at work, too. Specifically, if you have a need to always come across as the good guy or gal, you aren’t going to want to disappoint anyone or turn them off. If you are prone to feeling guilty, you won’t want to hurt anyone’s feelings.

Ladies and gentlemen, please accept the following rule: dating is risky business. Do not be a jerk to anyone you encounter, but don’t confuse that with being gently honest. Honesty is good, and you should be able to be honest without shattering your date’s self-esteem. After all, if this person is that fragile, he or she probably shouldn’t be dating. (They should be getting their emotional issues under control by reading and journaling, seeing a therapist, or talking to church or other professional staff.)

I will share a few examples of common awkward situations in dating, and I will give you some concrete examples of what to say and do so that you don’t have to feel stuck or frozen when any of these things happen to you.

You know you’re not interested, but your date starts making future plans.

While I believe that honesty is crucial in dating, there is a time and place for it. If you’re out on a date and you know that you’re not going to want to see the person again, it’s awkward when they start talking about future plans. They may say something like: “Have you heard about that movie? Maybe we could see that next week.” Alternatively, they may say something like this: “Do you have plans next weekend? I was thinking maybe we could [insert activity].” It would be very awkward to say no while you’re sitting across from your date at dinner, so don’t feel compelled to say no in that moment. Feel free to say something like,“That sounds interesting” or “Maybe that would work.” If your date brings the issue up at the end of the evening, that is a more appropriate time to address whether the two of you will keep seeing each other. Say, “Let’s see how the week unfolds and we can talk later.” If you want to be totally honest in the moment, say, “I’m not sure we’re a good fit, so is it okay if I pass? It was nice meeting you, though, and maybe we will be bump into each other in the future.”

Your date calls once, twice, or more after the last date, but you don’t want to see them again.

The kindest thing you can do is to think of your date’s feelings, even if you know that you are never going to go out with that person. Take the phone call when they call or call them back, and let them know that you are not interested. Do you believe this sounds harsh? If so, you either have guilt issues or you presume that this person is as fragile as a Faberge egg. When you talk on the phone – because you can do better than sending a callous text message – say, “I just wanted to call and say that I appreciated meeting you, but don’t think we’re a good fit for a relationship. I know I appreciate it when people are honest with me, so I wanted to extend you the same courtesy. I am glad I met you and hopefully we will cross paths in the future.” Not only is this behavior not selfish or mean, it is actually the most respectful, kind and grownup thing you can do. Why cause that other person to lay awake in bed at night thinking about you or wondering if you are interested when you can put their anxiety to rest with a three-minute conversation? If you were pining for someone who wasn’t interested in you, wouldn’t you rather know so you could move on and focus on someone or something else?

Your date goes in for a kiss and you, um, don’t want those lips to land on yours.

A good, simple rule: Never kiss anyone you don’t want to kiss. While this rule sounds silly or even nonsensical, the rule is rooted in a grim dating reality. Do you know how many men and women end up going along with a kiss (or even more) when they have no interest in the other person? Too often, people go along with things they don’t want to do because, again, they don’t know how to avoid it; they don’t like conflict; they feel guilty hurting someone’s feelings; or they have difficulty saying no. If your date goes in for a kiss on the mouth but you don’t have that desire yourself, simply turn your face and let them give you a kiss on the cheek. If they act offended or act like they’ve been rebuffed, smile and make a joke. Say, “Sorry, I’m shy” or “I’m shy about PDA.” Your date will understand that you don’t want to kiss them, and they will probably go home and tell themselves that you are not interested. If you are interested but just didn’t want to kiss them at that moment, call them later and make sure to let them know that you are interested in seeing them again.

Simple mantras to keep in mind as you date

It’s true that dating can bring a handful of awkward moments, but they don’t have to overwhelm you or turn you off altogether. A little bit of anxiety and awkwardness is part and parcel of dating. If you’re tuned in to your emotional needs and have realistic expectations, you will find a partner soon enough. Don’t get stuck feeling negative or tell yourself that you will be dating forever. The smarter you date now, the faster you will find a good partner. Remember that everyone gets rejected once in a while. Don’t worry about breaking anyone’s self-esteem and don’t let anyone destroy yours. You will find a lasting partner when you consistently put yourself in the right situations and invest in the prospects who are also investing in you.

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